O-Phenylenediamine → 4,4-Dimethyl-4H-5-oxa-1,3-dithia-6,11-diaza-cyclopenta[a]anthracen-2-one

HRID 887968Notes

Reaction equation

HRID 887968 reaction equation
[CH3:1][C:2]1([CH3:14])[C:7]2[S:8][C:9](=[O:11])[S:10][C:6]=2[C:5](=O)[C:4](=O)[O:3]1.[C:15]1([NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21].O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>>[CH3:1][C:2]1([CH3:14])[O:3][C:4]2[C:5](=[N:21][C:16]3[C:15]([N:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]2[S:10][C:9](=[O:11])[S:8][C:7]1=2

Participants

4

Reactant 3

HCID 7243O-PhenylenediamineHCID 591895774,4-dimethyl-4H-[1,3]dithiolo[4,5-c]pyran-2,6,7-trioneHCID 71586775Bentonite

Product 1

HCID 251667594,4-Dimethyl-4H-5-oxa-1,3-dithia-6,11-diaza-cyclopenta[a]anthracen-2-one

Procedure

4,4-Dimethyl-4H-[1,3]dithiolo[4,5-c]pyran-2,6,7-trione (5) (150 mg, 0.65 mmol), o-phenylenediamine (75 mg, 0.65 mmol) and montmorillonite KSF (100 mg) were mixed in a mortar until a homogeneous solid was obtained then the solid mixture was transferred into a test tube and irradiated with microwaves for 4 min. The resulting mixture was purified by chromatography (silica gel, CH2Cl2) to give pure 4,4-dimethyl-4H-5-oxa-1,3-dithia-6,11-diaza-cyclopenta[a]anthracen-2-one (7). Yield: 90 mg (45%).

Workup

  1. customwas obtained
  2. customthe solid mixture was transferred into a test tube
  3. customirradiated with microwaves for 4 min
  4. customThe resulting mixture was purified by chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-e25aad95788343e7ba485dce40e19d85
Source dataset
uspto-grants-2012_08
Patent number
US08247551B2

Reaction notes

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